[3+2] Cycloaddition-based one-pot synthesis of 3,9-diazabicyclo[4.2.1]nonane-containing scaffold

Zhang, Xiaofeng; Legris, Marc; Muthengi, Alex; Zhang, Wei

doi:10.1007/s10593-017-2072-2

Cited by 14 publications

(4 citation statements)

References 16 publications

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“…The azomethine ylides derived from deprotonation of iminium ions are CO 2 R-stabilized ylides A (Figure 2A) [22,23,24,25,26,27,28,29,30]. In recent years, our lab has reported a series of azomethine ylides A-based [3 + 2] cycloadditions for diverse heterocyclic scaffolds [31,32,33,34,35], including one-pot [3 + 2] and click reactions for triazolobenzodiazepines [32]. Compared to the reactions of stabilized ylides A, cycloadditions of nonstabilized ylides B are less explored (Figure 2B) [36,37,38,39,40,41,42].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions

Zhang

Qiu

et al. 2019

Molecules

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Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions

Zhang

Qiu

et al. 2019

Molecules

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“…1), it is speculated that introducing a tetrahedral spiro carbon can further improve bioactivity by providing structural rigidity 12 . Consequently, there have been numerous efforts made towards synthesizing heterocycles containing spirooxindole as the core structure [13][14][15][16][17][18] . Among different methodologies developed for synthesizing spirocyclic compounds 19,20 , the Michael addition is one of the most robust [21][22][23][24] .…”

Section: Highly Diastereoselective Cascade [5 + 1] Double Michael Rea...mentioning

confidence: 99%

Highly diastereoselective cascade [5 + 1] double Michael reaction, a route for the synthesis of spiro(thio)oxindoles

Moghaddam

Saberi

Karimi

2021

Sci Rep

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The first diastereoselective synthesis of spirothiooxindoles is reported via the Michael reaction between thiooxindoles and dibenzalacetones. The reaction was conducted without any catalyst or additive under green conditions, i.e., ethanol as the solvent and at room temperature. In addition, the described robust method benefits from scalability, simple work-up, and column chromatography-free purification. This work demonstrates the art of governing regio- and stereoselectivity, which has been discussed in the light of Density Functional Theory calculations. Our method represents the first synthesis of spiro[cyclohexanone-thiooxindoles] with the relative configuration of the aryl moieties at the cyclohexanone ring as cis. The obtained cis-spirothiooxindoles, can be used to afford cis-spirooxindoles, which their synthesis had not been explored before. According to our molecular docking studies, cis-spirooxindoles demonstrate higher binding affinities than corresponding trans-spirooxindoles for the OPRT domain of the Leishmania donovani uridine 5′-monophosphate synthase (LdUMPS). Thus, the reported method may eventually be utilized to develop new hit compounds for leishmaniasis treatment.

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“…For this reason, there have been numerous efforts towards the synthesis of heterocycles containing spiro oxindole as the core structure. [13][14][15][16][17][18] Among different methodologies that have been developed for the synthesis of spiro molecules, 19,20 the Michael addition is one of the most robust. [21][22][23][24] Recently, the organocatalytic cascade Michael addition has emerged as an efficient strategy to provide spirocyclic oxindole structures in one-pot.…”

Section: Introductionmentioning

confidence: 99%

Highly Diastereoselective Cascade [5+1] Double Michael Reaction, a Route for The Synthesis of Spiro Thio-Oxindoles

Moghaddam

Saberi

Karimi

2021

Preprint

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The first diastereoselective synthesis of spiro-thiooxindole is reported via Michael reaction between thiooxindoles and divinyl ketones. The reaction was conducted without any catalyst or additive under green conditions, i.e., ethanol as the solvent and room temperature. This study showed the art of governing regioselectivity in which novel spiro frameworks were generated in high yields. In addition to simple and column chromatography-free purification, the high diastereoselectivity makes this protocol very robust. The regio- and stereo- selectivity of the reaction has been discussed in light of the theoretical calculations, and molecular docking has been performed on the reaction products. Our method presents the first synthesis of cis-spiro thiooxindoles, which can be used to generate cis-spiro oxindoles. According to our docking studies, the latter demonstrates higher binding affinities towards the LdUMPS than corresponding trans-spiro oxindoles and may be utilized to develop new hit compounds for leishmaniasis treatment.

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[3+2] Cycloaddition-based one-pot synthesis of 3,9-diazabicyclo[4.2.1]nonane-containing scaffold

Cited by 14 publications

References 16 publications

One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions

One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions

Highly diastereoselective cascade [5 + 1] double Michael reaction, a route for the synthesis of spiro(thio)oxindoles

Highly Diastereoselective Cascade [5+1] Double Michael Reaction, a Route for The Synthesis of Spiro Thio-Oxindoles

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